The psychotherapeutic work is characterized by processes that are involved in the development of the alliance, as well as processes that lead to the ruptures in the alliance (error) and its repair. The purpose of this article is to highlight the clinical error that occurs when a clinician fails to adequately respond to a patient’s emotional signals due to countertransference reactions that results in an overemphasis on predetermined tasks the clinician “naturally” deems as necessary. A clinical vignette is presented to illustrate the error and 3 alternative approaches to the error are discussed. These include—(a) shared decision-making, (b) addressing and repairing alliance rupture, and (c) management of countertransference. Brief theoretical and clinical context for each alternative approach is provided.